Hydrochloric Acid → (Anthracen-1-yl)methanol

HRID 2413607Notes

Reaction equation

HRID 2413607 reaction equation
[C:1]1([C:15](O)=[O:16])[C:14]2[C:5](=[CH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.C1COCC1.CO.Cl>O>[C:1]1([CH2:15][OH:16])[C:14]2[C:5](=[CH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8028Tetrahydrofuran2×HCID 1507891-Anthracenecarboxylic Acid

Product 1

HCID 12695455(Anthracen-1-yl)methanolYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 500 mL 2-neck flask equipped with condenser, addition funnel with N2 inlet, and stirring bar was added 1-anthracenecarboxylic acid (6.88 g, 31 mmol) and dry THF (250 mL). To the addition funnel, was added a 1M solution of BH3 in THF (Aldrich, 50 mL, 50 mmol) via cannula. The BH3 solution was added over 1 h and the solution stirred overnight at RT. CH3OH was then added until H2 evolution ceased. H2O (5 mL) and then 1N HCl (5 mL) was added to the flask. The solvents were removed and then PhCH3 (100 mL) added to the flask. The PhCH3 was then also removed. The resulting solid was recrystallized from EtOAc/hexane to give 4.3 g (67%) of (1-anthryl)methanol mp 124°-125°, (C,H), (lit. 124°-125°, S. Akiyama et. al., Bull. Chem. Soc. Jap. 35 1826 (1962)).

Workup

  1. customTo a 500 mL 2-neck flask equipped with condenser, addition funnel with N2 inlet
  2. additionThe BH3 solution was added over 1 h
  3. stirringthe solution stirred overnight at RT
  4. customThe solvents were removed
  5. additionPhCH3 (100 mL) added to the flask
  6. customThe PhCH3 was then also removed
  7. customThe resulting solid was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-7e5cbd649c8648f49c7d04a1f6af90d8
Source dataset
uspto-grants-1988_01
Patent number
US04719047

Reaction notes

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