Acetic Anhydride → 4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzyl acetate

HRID 1382437Notes

Reaction equation

HRID 1382437 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH3:8][C:9]1([CH3:31])[CH2:18][CH2:17][C:16]([CH3:20])([CH3:19])[C:15]2[CH:14]=[C:13]([C:21]#[C:22][C:23]3[CH:30]=[CH:29]C(CO)=[CH:25][CH:24]=3)[CH:12]=[CH:11][C:10]1=2>N1C=CC=CC=1>[C:5]([O:4][CH2:1][C:2]1[CH:29]=[CH:30][C:23]([C:22]#[C:21][C:13]2[CH:12]=[CH:11][C:10]3[C:9]([CH3:31])([CH3:8])[CH2:18][CH2:17][C:16]([CH3:20])([CH3:19])[C:15]=3[CH:14]=2)=[CH:24][CH:25]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 539501414-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzyl alcohol

Product 1

HCID 197869654-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzyl acetateYield 77%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.7 ml of acetic anhydride were added to a mixture of 1.5 g (4.7 millimoles) of 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-ethynyl]-benzyl alcohol (Example 20) and 8.7 ml of pyridine. The mixture was stirred for 16 hours at room temperature, after which it was poured onto ice/water and acidified. The precipitated solid was filtered off under suction, washed with water and dried. 1.3 g (77%) of the title compound of melting point 136°-139° C. were obtained in this manner.

Workup

  1. additionafter which it was poured onto ice/water
  2. filtrationThe precipitated solid was filtered off under suction
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-d727886a23844f98b7289eaefe7151fb
Source dataset
uspto-grants-1989_02
Patent number
US04806558

Reaction notes

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