Acetic Anhydride → HCID 10909996, compound

HRID 1890141Notes

Reaction equation

HRID 1890141 reaction equation
[CH:1]1([C@H:7]([OH:9])[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:10](OC(=O)C)(=[O:12])[CH3:11]>C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:10]([O:9][C@@H:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:8])(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10290808(αR)-α-Methylcyclohexanemethanol

Product 1

HCID 10909996HCID 10909996, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Conditions

Temperature
35 °C

Procedure

A 2 L reaction flask was charged with (R)-1-cyclohexylethanol (980 g, synthesized as above), acetic anhydride (1 Kg), and p-toluene sulphonic acid (0.4 g), and heated at 30-40° C. for 6 hours. The reaction mixture was then transferred into a separatory funnel and washed twice in 200 mL water followed by once in 200 mL 10% sodium hydroxide (NaOH). The resulted organic layer was distilled at 5-10 mmHg to provide (R)-1-cyclohexylethyl acetate (1.3 Kg) (optical rotation: [α]D+2.59°; optical purity: 80.5% ee).

Workup

  1. customA 2 L reaction flask
  2. customThe reaction mixture was then transferred into a separatory funnel
  3. washwashed twice in 200 mL water
  4. distillationThe resulted organic layer was distilled at 5-10 mmHg

Sources & evidence

ORD record
ord-0328d4ec979b44dbaa2b832ace6802c5
Source dataset
uspto-grants-2013_08
Patent number
US08506943B2

Reaction notes

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