Toluene → 4-Benzyloxy-1-butanol

HRID 553263Notes

Reaction equation

HRID 553263 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([OH:13])[CH2:9][CH2:10][CH2:11][OH:12].[OH-].[Na+].C(Cl)C1C=CC=CC=1>O>[CH2:7]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][OH:13])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 7503Benzyl ChlorideHCID 80641,4-ButanediolHCID 14798Sodium Hydroxide

Product 1

HCID 5622124-Benzyloxy-1-butanolYield 53.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of toluene (50 ml), 1,4-butanediol (212 g, 2.35 mol) and sodium hydroxide (47.7 g) was heated up to 95° C., and thermally insulated at the same temperature for 30 minutes. Thereafter, benzyl chloride (150 g, 1.185 mol) was added and the mixture was thermally insulated at 95 to 105° C. for 4 hours, then, poured into water (250 ml). After neutralization with 35% hydrochloric acid, the organic layer was liquid-partitioned and the aqueous layer was extracted with toluene (100 ml). The organic layers were combined and washed with saline (100 ml). The organic layer was concentrated under reduced pressure, and the residue was distilled under reduced pressure, to obtain a title compound (115 g, yield 53.8%).

Workup

  1. waitthe mixture was thermally insulated at 95 to 105° C. for 4 hours
  2. customAfter neutralization with 35% hydrochloric acid, the organic layer was liquid-partitioned
  3. extractionthe aqueous layer was extracted with toluene (100 ml)
  4. washwashed with saline (100 ml)
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-b5004b4a0f4646c4be8068ec593b96ed
Source dataset
uspto-grants-2011_05
Patent number
US07951977B2

Reaction notes

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